Stepanov D. Synthesis and properties of 5,6,7,8-tetrahydro-4H-thiazolo[5,4-c]azepin-8-ones

Українська версія

Thesis for the degree of Candidate of Sciences (CSc)

State registration number

0404U004281

Applicant for

Specialization

  • 02.00.03 - Органічна хімія

21-10-2004

Specialized Academic Board

Д 41.219.02

Essay

Object of investigation: Thiazoloazepines, methods of synthesis and properties. Aim of investigation: elaboration of method of synthesis and study of properties of new type of condensate nitrogen containing heterocycles – 5,6,7,8-tetrahydro-4H-thiazolo[5,4-c]azepin-8-ones and theirs analogues. Methods of investigation and equipment: organic synthesis, IR, UV, NMR spectroscopy, mass spectrometry, elementary analysis, oncoming synthesis. Theoretical results and their novelty: Have been elaborated methods of synthesis of 5,6,7,8- tetrahydro-4H-thiazolo[5,4-c]azepin-8-ones from 4,5,6,7-tetra-hydrobenzothiazol-7ones; method of synthesis of 2-chlor-5,6,7,8-tetrahydro-4H-thiazolo[5,4-c]azepin-8-ones and 2-chlor-4,5,6,7-tetrahydrobenzothiazol-7ones by interaction between corresponding 2-aminoderivatives, amylnitrite and copper (II) chloride. Have been obtained several 2-R'R''N- и 2-R'O- substituted 5,6,7,8-tetrahydro-4H-thiazolo[5,4-c]azepin-8-ones and 4,5,6,7-tetrahydrobenzothiazol-7ones by interaction between the 2-chlorthiazoloazepinones ore 2-chlortiazolones and amines ore alcoholates respectively. Have been obtained 8-pyperidin-1-yl-5,6-dyhidro-4H- thiazolo[5,4-c]azepines by interaction between 5,6,7,8-tetrahydro-4H-thiazolo[5,4-c]azepin-8-tiones and pyperi-din in presence of HgCl2. Have been elaborated a method of synthesis of 8-aminoderivatives of new heterocyclic system – 5,6-dihidro-4H-bis[1,3]thiazolo [3,2-a:5',4'-c]azepin-7-ium by interaction between 5,6,7,8-tetrahydro-4H-thiazolo[5,4-c]azepin-8-tiones and chloroacetonitril. Antimicrobial activity of various derivatives of thiazoloazepinon and thiazolon haz been discovered. Practical results and their novelty: Methods of synthesis of 5,6,7,8- tetrahydro-4H-thiazolo[5,4-c]azepin-8-ones, of introduction of functional groups in the position 2 of thiazole cycle, of transformation of amide group of thiazoloazepines, of 5,6-dihidro-4H-bis[1,3]thiazolo[3,2-a:5',4'-c]azepin-7-ium, of thiazolones and theirs derivatives allow to put this results into practice ofthin organic synthesis. Results can be used in investigations of connection of structure and biological activity of organic compounds. Subject and the degree of introduction: publications, reports at the scientific conferences, using the results of work in the scientific and pedagogical practice of establishments of higher education and Scientific Research Institutes of Ukraine. Efficiency of introduction is provided by elaboration of preparative convenient method of synthesis of 5,6,7,8- tetrahydro-4H-thiazolo[5,4-c] azepin-8-ones and theirs derivatives. Sphere of use: chemistry.

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